This is more subtle than it seems at first glance. Many years ago I asked myself why we consider the free abelian group $C'_k(X)$ generated by all oriented $k$-simplices of $X$ and then form the quotient
$$C_k(X) = C'_k(X)/\langle \sigma + \overline{\sigma} \rangle$$
in which $\sigma$ and $-\overline{\sigma}$ are identified.
The group $C_k(X)$ is free abelian with one generator for each $k$-simplex $s$ of $X$. In other words, why do we start with two generators for each $k$-simplex $s$ (the two oriented simplices corresponding to $s$) of $X$ if we actually only want one?
The reason are the boundaries $\partial : C'_k(X) \to C'_{k-1}(X)$. On the generators we define $\partial(\sigma) = \sum_{i=0}^k (-1)^i \sigma_i$, where the $\sigma_i$ are the faces of $\sigma$ with the induced orientations. Unfortunately there is no reasonable way to define $\partial(s)$ for an unoriented simplex $s$. The problem are the signs which we have to associate to the faces $s_i$ of $s$. There is no canonical way to do so. In fact, there are two valid options which stem from the two orientations of $s$. However, to bypass this problem we can make a choice of an orientation for each $s$, subject to the condition that these choices are consistent over all simplices of $X$ (this means that if $s'$ is a face of a simplex $s$, then the orientation of $s'$ conincides with the orientation inherited from $s$). A nice way to do this is to choose a total ordering on the set of vertices of $X$. This gives us an ordering of the vertices of each simplex $s$, i.e. we can write $s = (p_0,\dots,p_k)$ in a unique order. This allows to define $\partial(s) = \sum_{i=0}^k (-1)^i s_i$, where $s_i$ is obbtained from $s$ be by deleting $p_i$. Let us denote the resulting chain complex by $C^{ord}_k(X)$. Recall that it involves a choice to form it.
It is a nice excercise to show that there exists a natural isomorphism $C^{ord}_*(X) \to C_*(X)$.
There is a similar issue with the cellular chain complex $D_k(X) = H_k(X_k,X_{k-1})$. These groups are free abelian with one generator for each $k$-simplex of $X$, but again it requires suitable choices to identify them with the generators of $C_k(X)$. To understand this let us look into the chapter about cellular homology in Hatcher's book "Algebraic topology", http://pi.math.cornell.edu/~hatcher/AT/AT.pdf. The boundaries can be computed via the "cellular boundary formula". This formula involves the characteristic maps of the $k$-cells $e_s$ in the form $\phi_s : S^{k-1} \to X_{k-1}$ (here $s$ is any $k$-simplex of $X$). But we only have a canonical attaching map $\iota_s : \partial \lvert s \rvert \hookrightarrow X_{k-1}$, where $\lvert s \rvert \subset\lvert X \rvert$ is the geometric realization of $s$. To get the characteristic maps in the desired form, we need a specific identification of $\lvert s \rvert$ with $D^k$. We may assume that $D^k$ is the standard $k$-simplex in $\mathbb{R}^{k+1}$ whose vertices are the standard base vectors $e_i$, but there are many homeomorphisms $D^k \to \lvert s \rvert$, so this involves a choice. To do this, we choose again a total ordering on the set of vertices of $X$. Then for each $s = (p_0,\dots,p_k)$ we get a canonical affine homeomorphism $h_s : D^k \to \lvert s \rvert$ such that $h_s(e_i) = p_i$. Then define $\phi_s = \iota_s h_s \mid_{S^{k-1}}$. For the sake of clarity let us write $D^{ord}_*(X)$ for the resulting cellular chain complex.
Now $X_k/X_{k-1}$ is a wedge of $k$-spheres and thus each $\phi_s$ determines a generator of $D^{ord}_k(X)$ by identifying $S^k$ with one of spheres in this wedge ($\phi_s$ induces $\phi'_s : S^k = D^k/S^{-1} \to X_k/X_{k-1}$ and we take $(\phi'_s)_*(g_k) \in D^{ord}_k(X)$, where $g_k$ is a generator of $H_k(S^k)$).
Now define isomorphisms $f_k : C^{ord}_k(X) \to D^{ord}_k(X), f_k(s) = (\phi'_s)_*(g_k)$. It is a nice exercise (based on Hatcher) to verify that the $f_k$ constitute a chain map $f_* : C^{ord}_*(X) \to D^{ord}_*(X)$.