Let $\mathbb{E}^1$ denote $\mathbb{R}$ equipped with the standard Euclidean topology. Let $X$ denote $\mathbb{R}$ with the topology for which a nonempty subset $U \subset \mathbb{R}$ is open if and only if its complement $\mathbb{R} \backslash U$ is compact as a subspace of $\mathbb{E}^1$. This is called the compact complement topology in [SS].
Question: Is $X$ simply connected?
To paint a bit of a picture, note that the topology on $X$ is coarser than the Euclidean topology. This means that the identity function $\mathbb{E}^1 \to X$ is continuous, so it clearly follows that $X$ is arc-connected (each pair of distinct points is connected by an injective path $[0, 1] \to X$). The topology on $X$ is finer than the finite complement topology on $\mathbb{R}$, for which nonempty open sets are exactly the complements of finite sets; this is equivalent to $X$ being $T_1$ [SS, Item 1]. Observe also that $X$ has no disjoint nonempty open subsets, which means it is hyperconnected (= irreducible) [SS, Item 3]. It easily follows from hyperconnectedness that $X$ is not Hausdorff. Unlikely, but perhaps it's relevant to mention that $X$ is compact, since the complement of any chosen set in an open cover is compact, so finitely many of the others plus the chosen set must cover $X$ [SS, Item 4].
This answer in the thread Path-connected subsets of compact complement topology says that any subset of $X$ containing an unbounded interval is path-connected, and speculates that a set which does not contain an unbounded interval is path-connected if and only if it is path-connected as a subspace of $\mathbb{E}^1$. Taking this for granted, it seems like the idea may be that the path $[0, 1] \to X$ from $0$ to $1$ which is the restriction of the identity function shouldn't be path homotopic to a path from $0$ to $1$ with image $(-\infty, 0] \cup \{1\}$, but I don't know how to argue this.
The thread Is the compact complement topology locally arc connected? may also have potentially useful information.
It may be interesting to compare with superficially similar spaces. I.e,
- The finite complement topology on $\mathbb{R}$ is contractible. See here.
- The countable complement topology on $\mathbb{R}$, for which open sets are the empty set and the complements of countable sets, is connected but not even path-connected. See this answer.
[SS] Steen, L. A.; Seebach, J. A. jun., Counterexamples in topology, New York etc.: Holt, Rinehart and Winston, Inc., XIII, 210 p. (1970). ZBL0211.54401.